4-(3,4-Dinitrobenzyl)morpholine → 4-(Morpholinomethyl)benzene-1,2-diamine

HRID 1012134Notes

Reaction equation

HRID 1012134 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O>[Fe].O1CCOCC1.O>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:16]([NH2:17])=[CH:15][CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholine

Product 1

HCID 251933094-(Morpholinomethyl)benzene-1,2-diamineYield 73%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a mixture of 4-(3,4-dinitro-benzyl)-morpholine (2.5 g, 9.3 mmol), Fe powder (5.2 g, 93 mmol) and FeSO4.7H2O (1.3 g, 4.6 mmol) was added 1,4-dioxane:water (5:1, 60 ml). The mixture was refluxed for 3 h, filtered through celite, washing with MeOH, and reduced in vacuo azeotroping with toluene. EtOAc (100 ml) was added and insoluble material removed via filtration. The filtrate was reduced in vacuo to give 4-morpholin-4-ylmethyl-benzene-1,2-diamine as a dark brown solid (1.4 g, 73%). (LC/MS: Rt 0.40, no ionization).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationfiltered through celite
  3. washwashing with MeOH
  4. customazeotroping with toluene
  5. additionEtOAc (100 ml) was added
  6. custominsoluble material removed via filtration

Sources & evidence

ORD record
ord-1948c158d8bb4af5a32448986e7bfc9e
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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